3-(4-(Benzo[d]thiazol-2-yl)-1-phenyl-1H-pyrazol-3-yl) phenyl acetate induced Hep G2 cell apoptosis through a ROS-mediated pathway

Chemico-Biological Interactions

Volumn 183, Issue 3, 2010, Pages 341-348

  Li, Jianyong ^a   Xu, Zhijun ^b   Tan, Mengyao ^a   Su, Weike ^b   Gong, Xing guo ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Apoptosis; Benzothiazole; Caspase; DPB 5; ROS

Indexed keywords

3 [4 (BENZO[D]THIAZOL 2 YL) 1 PHENYL 1H PYRAZOL 3 YL]PHENYL ACETATE; BENZOTHIAZOLE DERIVATIVE; CASPASE 9; GLUTATHIONE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL STRAIN HEPG2; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA FRAGMENTATION; DRUG CYTOTOXICITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; MITOCHONDRIAL ENERGY TRANSFER; MITOCHONDRIAL MEMBRANE POTENTIAL;

APOPTOSIS; BENZOTHIAZOLES; CASPASE 9; DRUG SCREENING ASSAYS, ANTITUMOR; GLUTATHIONE; HEP G2 CELLS; HUMANS; MEMBRANE POTENTIAL, MITOCHONDRIAL; PYRAZOLES; REACTIVE OXYGEN SPECIES;

EID: 74149087636     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2009.12.008     Document Type: Article

References (45)

1. Qin Y., Chen F.D., Zhou L., Gong X.G., and Han Q.F. Proliferative and anti-proliferative effects of thymosin alpha1 on cells are associated with manipulation of cellular ROS levels. Chem. Biol. Interact. 180 (2009) 383-388
2. Fadeel B., Orrenius S., and Zhivotovsky B. Apoptosis in human disease: a new skin for the old ceremony?. Biochem. Biophys. Res. Commun. 266 (1999) 699-717
3. Thompson C.B. Apoptosis in the pathogenesis and treatment of disease. Science 267 (1995) 1456-1462
4. Hu W., and Kavanagh J.J. Anticancer therapy targeting the apoptotic pathway. Lancet Oncol. 4 (2003) 721-729
5. Rohayem J., Diestelkoetter P., Weigle B., Oehmichen A., Schmitz M., Mehlhorn J., Conrad K., and Rieber E.P. Antibody response to the tumor-associated inhibitor of apoptosis protein survivin in cancer patients. Cancer Res. 60 (2000) 1815-1817
6. LaCasse E.C., Baird S., Korneluk R.G., and MacKenzie A.E. The inhibitors of apoptosis (IAPs) and their emerging role in cancer. Oncogene 17 (1998) 3247-3259
7. Murrell G.A., Francis M.J., and Bromley L. Modulation of fibroblast proliferation by oxygen free radicals. Biochem. J. 265 (1990) 659-665
8. Buttke T.M., and Sandstrom P.A. Oxidative stress as a mediator of apoptosis. Immunol. Today 15 (1994) 7-10
9. Martin K.R., and Barrett J.C. Reactive oxygen species as double-edged swords in cellular processes: low-dose cell signaling versus high-dose toxicity. Hum. Exp. Toxicol. 21 (2002) 71-75
10. Lu M., Gong X., Lu Y., Guo J., Wang C., and Pan Y. Molecular cloning and functional characterization of a cell-permeable superoxide dismutase targeted to lung adenocarcinoma cells. Inhibition cell proliferation through the Akt/p27kip1 pathway. J. Biol. Chem. 281 (2006) 13620-13627
11. Green D.R., and Reed J.C. Mitochondria and apoptosis. Science 281 (1998) 1309-1312
12. Simon H.U., Haj-Yehia A., and Levi-Schaffer F. Role of reactive oxygen species (ROS) in apoptosis induction. Apoptosis 5 (2000) 415-418
13. Mallis R.J., Buss J.E., and Thomas J.A. Oxidative modification of H-ras: S-thiolation and S-nitrosylation of reactive cysteines. Biochem. J. 355 (2001) 145-153
14. Ames B.N. Endogenous DNA damage as related to cancer and aging. Mutat. Res. 214 (1989) 41-46
15. Schumacker P.T. Reactive oxygen species in cancer cells: live by the sword, die by the sword. Cancer Cell 10 (2006) 175-176
16. Pelicano H., Carney D., and Huang P. ROS stress in cancer cells and therapeutic implications. Drug Resist. Update 7 (2004) 97-110
17. Karthikeyan M.S. Synthesis, analgesic, anti-inflammatory and antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles. Eur. J. Med. Chem. 44 (2009) 827-833
18. Tricot G.J., Jayaram H.N., Lapis E., Natsumeda Y., Nichols C.R., Kneebone P., Heerema N., Weber G., and Hoffman R. Biochemically directed therapy of leukemia with tiazofurin, a selective blocker of inosine 5′-phosphate dehydrogenase activity. Cancer Res. 49 (1989) 3696-3701
19. Olah E., Natsumeda Y., Ikegami T., Kote Z., Horanyi M., Szelenyi J., Paulik E., Kremmer T., Hollan S.R., Sugar J., et al. Induction of erythroid differentiation and modulation of gene expression by tiazofurin in K-562 leukemia cells. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 6533-6537
20. Coll M., Frederick C.A., Wang A.H., and Rich A. A bifurcated hydrogen-bonded conformation in the d(A.T) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 8385-8389
21. Kopka M.L., Yoon C., Goodsell D., Pjura P., and Dickerson R.E. The molecular origin of DNA-drug specificity in netropsin and distamycin. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 1376-1380
22. Einhorn L.H., and Donohue J. Cis-diamminedichloroplatinum, vinblastine, and bleomycin combination chemotherapy in disseminated testicular cancer. Ann. Intern. Med. 87 (1977) 293-298
23. Sharma P., and Ghoshal N. Exploration of a binding mode of benzothiazol-2-yl acetonitrile pyrimidine core based derivatives as potent c-Jun N-terminal kinase-3 inhibitors and 3D-QSAR analyses. J. Chem. Inf. Model. 46 (2006) 1763-1774
24. Guedat P., and Colland F. Patented small molecule inhibitors in the ubiquitin proteasome system. BMC Biochem. 8 Suppl. 1 (2007) S14
25. Choi S.J., Park H.J., Lee S.K., Kim S.W., Han G., and Choo H.Y. Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity. Bioorg. Med. Chem. 14 (2006) 1229-1235
26. Pinar A., Yurdakul P., Yildiz I., Temiz-Arpaci O., Acan N.L., Aki-Sener E., and Yalcin I. Some fused heterocyclic compounds as eukaryotic topoisomerase II inhibitors. Biochem. Biophys. Res. Commun. 317 (2004) 670-674
27. Prouillac C., Vicendo P., Garrigues J.C., Poteau R., and Rima G. Evaluation of new thiadiazoles and benzothiazoles as potential radioprotectors: free radical scavenging activity in vitro and theoretical studies (QSAR, DFT). Free Radic. Biol. Med. 46 (2009) 1139-1148
28. Temiz-Arpaci O., Coban T., Tekiner-Gulbas B., Can-Eke B., Yildiz I., Aki-Sener E., Yalcin I., and Iscan M. A study on the antioxidant activities of some new benzazole derivatives. Acta. Biol. Hung. 57 (2006) 201-209
29. Repicky A., Jantova S., and Cipak L. Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-amino-acrylonitrile in human leukemia cells involves ROS-mitochondrial mediated death signaling and activation of p38 MAPK. Cancer Lett. 277 (2009) 55-63
30. Shi Y., Wang C.H., and Gong X.G. Apoptosis-inducing effects of two anthraquinones from Hedyotis diffusa WILLD. Biol. Pharm. Bull. 31 (2008) 1075-1078
31. Mian M.F., Kang C., Lee S., Choi J.H., Bae S.S., Kim S.-H., Kim Y.-H., Ryu S.H., Suh P.-G., Kim J.-S., and Kim E. Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis. Chem. Biol. Interact. 171 (2008) 57-66
32. Orwar O., Fishman H.A., Ziv N.E., Scheller R.H., and Zare R.N. Use of 2,3-naphthalenedicarboxaldehyde derivatization for single-cell analysis of glutathione by capillary electrophoresis and histochemical localization by fluorescence microscopy. Anal. Chem. 67 (1995) 4261-4268
33. Hartree E.F. Determination of protein: a modification of the Lowry method that gives a linear photometric response. Anal. Biochem. 48 (1972) 422-427
34. Scarlett J.L., Sheard P.W., Hughes G., Ledgerwood E.C., Ku H.H., and Murphy M.P. Changes in mitochondrial membrane potential during staurosporine-induced apoptosis in Jurkat cells. FEBS Lett. 475 (2000) 267-272
35. Ly J.D., Grubb D.R., and Lawen A. The mitochondrial membrane potential (deltapsi(m)) in apoptosis; an update. Apoptosis 8 (2003) 115-128
36. Xiong Y., Liu X., Lee C.P., Chua B.H., and Ho Y.S. Attenuation of doxorubicin-induced contractile and mitochondrial dysfunction in mouse heart by cellular glutathione peroxidase. Free Radic. Biol. Med. 41 (2006) 46-55
37. Lopez E., Arce C., Oset-Gasque M.J., Canadas S., and Gonzalez M.P. Cadmium induces reactive oxygen species generation and lipid peroxidation in cortical neurons in culture. Free Radic. Biol. Med. 40 (2006) 940-951
38. Hennet T., Richter C., and Peterhans E. Tumour necrosis factor-alpha induces superoxide anion generation in mitochondria of L929 cells. Biochem. J. 289 (1993) 587-592
39. Inoue M., Sato E.F., Nishikawa M., Park A.M., Kira Y., Imada I., and Utsumi K. Mitochondrial generation of reactive oxygen species and its role in aerobic life. Curr. Med. Chem. 10 (2003) 2495-2505
40. Shi Y. Mechanisms of caspase activation and inhibition during apoptosis. Mol. Cell 9 (2002) 459-470
41. Rhee S.G., Yang K.S., Kang S.W., Woo H.A., and Chang T.S. Controlled elimination of intracellular H(2)O(2): regulation of peroxyredoxin, catalase, and glutathione peroxidase via post-translational modification. Antioxid. Redox Signal. 7 (2005) 619-626
42. Higuchi Y. Glutathione depletion-induced chromosomal DNA fragmentation associated with apoptosis and necrosis. J. Cell Mol. Med. 8 (2004) 455-464
43. Giorgio M., Migliaccio E., Orsini F., Paolucci D., Moroni M., Contursi C., Pelliccia G., Luzi L., Minucci S., Marcaccio M., Pinton P., Rizzuto R., Bernardi P., Paolucci F., and Pelicci P.G. Electron transfer between cytochrome c and p66Shc generates reactive oxygen species that trigger mitochondrial apoptosis. Cell 122 (2005) 221-233
44. Nemoto S., Combs C.A., French S., Ahn B.H., Fergusson M.M., Balaban R.S., and Finkel T. The mammalian longevity-associated gene product p66shc regulates mitochondrial metabolism. J. Biol. Chem. 281 (2006) 10555-10560
45. Kok S.H., Gambari R., Chui C.H., Yuen M.C., Lin E., Wong R.S., Lau F.Y., Cheng G.Y., Lam W.S., Chan S.H., Lam K.H., Cheng C.H., Lai P.B., Yu M.W., Cheung F., Tang J.C., and Chan A.S. Synthesis and anti-cancer activity of benzothiazole containing phthalimide on human carcinoma cell lines. Bioorg. Med. Chem. 16 (2008) 3626-3631